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Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry
| Title: | Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry |
| Authors: | Takahashi, Rikuro Browse this author | | Seo, Tamae Browse this author | | Kubota, Koji Browse this author | | Ito, Hajime Browse this author →KAKEN DB |
| Keywords: | mechanochemistry | | cross-coupling | | polyfluoroarylation | | ball mill | | synthesis |
| Issue Date: | 29-Nov-2021 |
| Publisher: | American Chemical Society |
| Journal Title: | ACS catalysis |
| Volume: | 11 |
| Issue: | 24 |
| Start Page: | 14803 |
| End Page: | 14810 |
| Publisher DOI: | 10.1021/acscatal.1c03731 |
| Abstract: | The Suzuki-Miyaura cross-coupling between poly-fluorinated arylboron nucleophiles and aryl halides enables the efficient construction of polyfluorinated structural motifs frequently found in organic materials and catalysts. A key challenge associated with this transformation involves the slow transmetalation with weakly nucleophilic polyfluorinated organoboron reagents, which often reduces the yield of the coupling products. Here, we show that solid-state high-temperature ball-milling conditions facilitate a palladium-catalyzed cross-coupling with polyfluorinated arylboronic acids and pinacol esters employing a simple catalytic system in the absence of any stoichiometric additives. This reaction exhibits a broad substrate scope and can be carried out in air, and the use of large amounts of dry and degassed organic solvents is not required. The successful cross-coupling of weakly nucleophilic polyfluorinated organoboron reagents was ascribed to the extremely high concentrations of the substrates and the catalyst under solid-state conditions. |
| Rights: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/articlesonrequest/AOR-DV535GSW7VUYJFNAH5DM. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/87310 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 久保田 浩司
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